Azo dyestuffs and their manufacture



the corresponding 2-hydroxynaphthalene-'l-sulfonic acid derivatives are very similar to the dyestuff above described.

The dyestuis enumerated in the following table are also prepared according to the indications cited in the above examples.

2-hydroxynaphthalene 4 sulfonc acid amide- (N-methylene carboxylic acid) M. P. 197- 198 C.

2hydroxynaphthalene 4 sulfonic acid amide- Y(N-phenyD-(N-methylene carboxylic acid) M.

P. 24U-241 C.

Dyeing on wool Example Diazo component zo component Aiter-chromcd Acid or treated according to the one-bath process 3 5-nitro2amino-l-hydroxy-benzene. 2-hydroxynaphthalene-4-sulfonic acid amide(N-methyl Wine-red Grey-blue.

ene carboxylic acid). 4 do 2-hydroxynaphthalene-4-sulfonic acid amlde-(N-pbenyD- Dark winc- Do.

(N-methylene carboxylic acid). v red. I 5 6chloro4-nltro-2-amino-l-hy- 2hydroxynap-htbalene4sulfonic acid amide-(N-methyl- Black Brown-violet.

droxy-benzene. ene carboxylic acid). 6 do 2-hydroxynaphthalene-4-sulfonic acid amide-(N-phenyD- do Dull black.

(N-methylene carboxylic acid). 4:6-dinitro-2-amino-l -hydroxy- 2-hydroxynaphthalene4ieulionic acid amide-(N -methyl- Brown-red. Violet-brown.

benzene. ene carboxylic acid). do 2-hydroxynaphthalene-dsu1fonieacid amide(N-phenyl) do Brownviolet.

(N-methylene carboxylic acid). 4:6-dichloro-2-amino-l-hydroxy- 1hydroxynaphthalene-4-sulfonic acid amide-(N-methyl Red Violet.

benzene. ene carboxylic acid). 4:6-dinitro-2-amino-l -hydroxyl-hydroxynapbthalene5-sulionic acid amide-(N-methyl- Brown Black.

benzene. ene carboxylic acid). -do l-hydroxynaphthalcne--sulionie acid amide(N-phenyl) .do Greenish-black.

' (N-mcthylene carboxylic acid).

naphthalene-l-sulfonic acid amide-(-methylene carboxylic acid ethyl ester) with the calculated quantity of alkali there is obtained the 2- hydroxynaphthalene-4-sulfonic acid amide-(N- methylene carboxylic acid) which can be isolated by acidifying with mineral acid in form of the free acid or, after neutralization, by salting out in form of its monoalkali salt.V

Some of the new hydroxynaphthalene sulfonic acid amide derivatives are distinguished by a good crystallizing power, such as especially the derivatives of the 2-hydroxynaphthalene-l-sulfonic acid amide and of the Z-hydroxynaphthalene--sulfonic acid amide. The derivatives of the l-hydroxynaphthalene-ior -5-sulfonic acid r amide, especially in the form ofcarboxylic acid esters, form diillcultlyv crystallizing resins; the saponlfication products thereof, however, can in most cases easily be obtained by salting out in form of the crystalline monosodium salts.

Finally, someY of the new compounds may be characterized by their melting points:

2 carbomethoxy-hydroxynaphthalene-i-sulfonic acid amide-(N-methylene carboxylic acid ethyl ester) M. P. 1181l9 C.

2 carbomethoxy-hydroxynaphthalene-4-sulfonic acid amide-(N phenyl) (N methylene carboxylic acid ethyl ester) M. P. 11B-119 C.

2.- carbomethOxy-hydroxynaphthalene--sulfonic i acid amide-(N methylene carboxylic acid ethyl ester) M; P; 10Q-110 C.

2 carbomethoXy-hydroxynaphthalene6-sulfonic acid amide-(N phenyl) (N methylene carboxylic acid ethyl ester) M. P. 10S-104 C.

2-hydroxynaphthalene 6 sulfonic acid amide- (N-methylene carboxylic acid) M. P. 20'1- 209 C.

Z-hydroxynaphthalene 6 sulfonic acid amide- (N-phenyl) (N-methylene carboxylic acid) M. P. 203 C.

l-hydroxynaphthalene 5 sulfonic acid amide- (N-methylene carboxylic acid) M. P. 194- 195 C.

What we claim is:

l. Process for the manufacture of o-hydroxy azo dyestuis consistingin coupling a member of the group consisting of diazotized 2-amino-lphenols substituted by a member of the group consisting of halogen and nitro and diazotized 2- aminobenzene-l-carboxylic acids with a hydroxynaphthalene sulfonic acid amide, coupling in o-position to the hydroxy group, of the general formula CH2.COOH

wherein X 'means a member of the group consisting of H, lower alkyl and aryl of the benzene series.

2. The o-hydroxy azo dyestuils having in the free state the following general formula wherein X means a member of the group consisting of H, lower alkyl and aryl of the benzene series, Y means a member of the group consisting of OH and COOH, Z means a member of the group consisting `of H, halogen and nitro, Z being only H when nY is a carboxyl group and n being one of the numbers l and 2, the azo group Vand the hydroxy group inthe naphthalene nucleus being in o-position to each other.

3. The o-hydroxy azo dyestufs having in the free state the following general formula wherein X means a member of the group consisting of H, lower alkyl and aryl of the benzene series, the azo group and the hydroxy group in the naphthalene nucleus being in o-position to each other.

5. The o-hydroxy azo dyestuffs having in the free state the following general formula wherein X means a member of the group consisting of H, lower alkyl and aryl of the benzene series, the azo group and the hydroxy group in the naphthalene nucleus being in o-position to each other.

6. Theo-hydroxy azo dyestul having in the free state the following formula SOz.N.CHzC 00H 10 being when neutralized and dried a red powder,

dyeing wool according to the one-bath or afterchroming method with full red shades of excellent fulling, potting and light fastness.

7, The o-hydroxy azo dyestuff having in the 15 free state the following formula being when neutralized and dried a dark, bronz- 25 ing powder dyeing wool according to the onebath chroming method with'iull grey-blue shades of excellent fulling, potting and light fastness.

8. The o-hydroxy azo dyestuf having in the free state the following formula SO2.NH.CH2C O OH dyeing wool from an acid bath in red shades which by after-treatment with bichromate change to violet shades of excellent fastness properties.

ACHILLE CONZE'ITI. GUIDO SCHETTY. 

